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FR2314910A1 - Aldehyde prepn. by olefine hydroformylation in liquid phase - using catalyst system contg. sulphonated aryl phosphine and rhodium (NL 22.12.76) - Google Patents

Aldehyde prepn. by olefine hydroformylation in liquid phase - using catalyst system contg. sulphonated aryl phosphine and rhodium (NL 22.12.76)

Info

Publication number
FR2314910A1
FR2314910A1 FR7519407A FR7519407A FR2314910A1 FR 2314910 A1 FR2314910 A1 FR 2314910A1 FR 7519407 A FR7519407 A FR 7519407A FR 7519407 A FR7519407 A FR 7519407A FR 2314910 A1 FR2314910 A1 FR 2314910A1
Authority
FR
France
Prior art keywords
hydroformylation
catalyst system
prepn
olefine
rhodium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7519407A
Other languages
French (fr)
Other versions
FR2314910B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7519407A priority Critical patent/FR2314910A1/en
Priority to US05/696,909 priority patent/US4248802A/en
Priority to DE2627354A priority patent/DE2627354C3/en
Priority to JP51072077A priority patent/JPS5912091B2/en
Priority to ES449003A priority patent/ES449003A1/en
Priority to NLAANVRAGE7606634,A priority patent/NL182397C/en
Priority to IT50003/76A priority patent/IT1069268B/en
Priority to GB25463/76A priority patent/GB1540242A/en
Priority to BE168124A priority patent/BE843177A/en
Priority to CA255,250A priority patent/CA1074337A/en
Priority to BR7603941A priority patent/BR7603941A/en
Publication of FR2314910A1 publication Critical patent/FR2314910A1/en
Application granted granted Critical
Publication of FR2314910B1 publication Critical patent/FR2314910B1/fr
Priority to JP57025837A priority patent/JPS57167937A/en
Priority to US06/393,439 priority patent/USRE31812E/en
Priority to CA000419725A priority patent/CA1152105B/en
Granted legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aldehydes are prepd. by liq. phase hydroformylation of aliphatic olefines with CO and H2 in the presence of a catalyst. The catalyst consists of an aq. soln. contg. RH as metal or cpd. and >=1 sulphonated phosphine having formula (I) Ar1, Ar2 and Ar3 are aryl. Y1, Y2, Y3 are 1-4C alkyl or alkoxy, halogen -OH, -CN, -NO2 or -NR1R2, in which R1 and R2 are 1-4C alkyl. M is a solubilising cation consisting of alkali(ne) earth metals, Pb, Zn, Cu NH4 or N(R3R4R5R6)+, in which R3, R4, R5, R6 are 1-4C alkyl. m1, m2, m3 are integers 0 to 5, n1, n2, n3 are integers 0 to 3, provided >=1 of n1, n2, n3 is >=1. Aldehydes are obtd. in high yields. Reaction selectivity is >=90%. Hydroformylation prods. are easily sepd. from reaction medium. Catalyst system can be recovered without loss in activity.
FR7519407A 1975-06-20 1975-06-20 Aldehyde prepn. by olefine hydroformylation in liquid phase - using catalyst system contg. sulphonated aryl phosphine and rhodium (NL 22.12.76) Granted FR2314910A1 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
FR7519407A FR2314910A1 (en) 1975-06-20 1975-06-20 Aldehyde prepn. by olefine hydroformylation in liquid phase - using catalyst system contg. sulphonated aryl phosphine and rhodium (NL 22.12.76)
US05/696,909 US4248802A (en) 1975-06-20 1976-06-17 Catalytic hydroformylation of olefins
CA255,250A CA1074337A (en) 1975-06-20 1976-06-18 Process for the hydroformylation of olefins
ES449003A ES449003A1 (en) 1975-06-20 1976-06-18 Catalytic hydroformylation of olefins
NLAANVRAGE7606634,A NL182397C (en) 1975-06-20 1976-06-18 PROCESS FOR HYDROFORMYLATING ORGANIC COMPOUNDS CONTAINING AT LEAST A DOUBLE CARBON-CARBON CONNECTION.
IT50003/76A IT1069268B (en) 1975-06-20 1976-06-18 HYDROFORMULATION PROCEDURE FOR OLEFINS
DE2627354A DE2627354C3 (en) 1975-06-20 1976-06-18 Process for the production of aldehydes
BE168124A BE843177A (en) 1975-06-20 1976-06-18 OLEFINS HYDROFORMYLATION PROCESS
JP51072077A JPS5912091B2 (en) 1975-06-20 1976-06-18 Hydroformylation method of olefin
BR7603941A BR7603941A (en) 1975-06-20 1976-06-18 OLEFIN HYDROFORMILLATION PROCESS
GB25463/76A GB1540242A (en) 1975-06-20 1976-06-18 Process for the hydroformylation of olefines
JP57025837A JPS57167937A (en) 1975-06-20 1982-02-19 Hydroformylation of olefin
US06/393,439 USRE31812E (en) 1975-06-20 1982-06-29 Catalytic hydroformylation of olefins
CA000419725A CA1152105B (en) 1975-06-20 1983-01-18 Hydroformylation process of olefins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7519407A FR2314910A1 (en) 1975-06-20 1975-06-20 Aldehyde prepn. by olefine hydroformylation in liquid phase - using catalyst system contg. sulphonated aryl phosphine and rhodium (NL 22.12.76)

Publications (2)

Publication Number Publication Date
FR2314910A1 true FR2314910A1 (en) 1977-01-14
FR2314910B1 FR2314910B1 (en) 1977-12-02

Family

ID=9156817

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7519407A Granted FR2314910A1 (en) 1975-06-20 1975-06-20 Aldehyde prepn. by olefine hydroformylation in liquid phase - using catalyst system contg. sulphonated aryl phosphine and rhodium (NL 22.12.76)

Country Status (3)

Country Link
JP (1) JPS57167937A (en)
BE (1) BE843177A (en)
FR (1) FR2314910A1 (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009150A1 (en) * 1978-09-15 1980-04-02 BASF Aktiengesellschaft Process for the preparation of aldehydes
FR2550202A1 (en) * 1983-08-03 1985-02-08 Rhone Poulenc Rech PROCESS FOR THE PREPARATION OF TRI (M-SULFOPHENYL) PHOSPHINE
FR2561650A1 (en) * 1984-03-26 1985-09-27 Rhone Poulenc Rech IMPROVEMENT TO THE PROCESS FOR THE PREPARATION OF TRI (M-SULFOPHENYL) PHOSPHINE BY HYDROLYSIS AND CONTROLLED DILUTION OF SULFONATE
EP0157316A2 (en) * 1984-04-03 1985-10-09 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0160249A2 (en) * 1984-04-28 1985-11-06 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0163234A2 (en) * 1984-06-01 1985-12-04 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0216151A2 (en) * 1985-08-29 1987-04-01 Hoechst Aktiengesellschaft Process for the preparation of 2-ethyl hexanol
EP0226988A2 (en) * 1985-12-24 1987-07-01 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0255673A2 (en) * 1986-08-06 1988-02-10 Hoechst Aktiengesellschaft Process for the recovery of rhodium from aqueous solutions containing rhodium complex compounds
EP0302375A2 (en) * 1987-08-06 1989-02-08 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0372615A2 (en) * 1988-11-28 1990-06-13 Virginia Tech Intellectual Properties, Inc. Hydroformylation process
EP0621075A2 (en) * 1993-04-19 1994-10-26 Kuraray Co., Ltd. Novel rhodium-containing catalyst
BE1008019A3 (en) * 1994-01-07 1995-12-12 Dsm Nv Process for the preparation of an aldehyde.
EP0776880A1 (en) 1995-11-30 1997-06-04 Institut Francais Du Petrole Process for the hydroformylation of olefinic compounds
WO1998030527A1 (en) * 1997-01-13 1998-07-16 Celanese Gmbh Process for preparing aldehydes by hydroformylation
WO1999013982A1 (en) * 1997-09-16 1999-03-25 Celanese Chemicals Europe Gmbh Method for preparing aldehydes by hydroformylation
EP0924218A1 (en) * 1997-12-22 1999-06-23 Celanese GmbH Non aqueous ionogen liquid ligands, process for their preparation and their use as components for catalysts
WO1999060003A1 (en) * 1998-05-20 1999-11-25 Rhodia Fiber And Resin Intermediates Novel furylphosphines and organometallic complexes containing them

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3534317A1 (en) * 1985-09-26 1987-04-02 Ruhrchemie Ag METHOD FOR PRODUCING NONADECANDIOLES
US5307024A (en) * 1992-07-27 1994-04-26 Tektronix, Inc. Linearized level-shifting amplifier
JP5732379B2 (en) 2011-11-30 2015-06-10 株式会社キトー Link for chain connection

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NEANT *

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009150A1 (en) * 1978-09-15 1980-04-02 BASF Aktiengesellschaft Process for the preparation of aldehydes
FR2550202A1 (en) * 1983-08-03 1985-02-08 Rhone Poulenc Rech PROCESS FOR THE PREPARATION OF TRI (M-SULFOPHENYL) PHOSPHINE
EP0133410A1 (en) * 1983-08-03 1985-02-20 Rhone-Poulenc Recherches Process for preparing tri(M-sulphophenyl)phosphine
FR2561650A1 (en) * 1984-03-26 1985-09-27 Rhone Poulenc Rech IMPROVEMENT TO THE PROCESS FOR THE PREPARATION OF TRI (M-SULFOPHENYL) PHOSPHINE BY HYDROLYSIS AND CONTROLLED DILUTION OF SULFONATE
EP0158572A1 (en) * 1984-03-26 1985-10-16 Rhone-Poulenc Recherches Process for preparing tri(M-sulfophenyl)phosphine by hydrolysis and controlled dilution of the sulfonation mixture
EP0157316A3 (en) * 1984-04-03 1987-05-27 Ruhrchemie Aktiengesellschaft Process for the preparation of aldehydes
EP0157316A2 (en) * 1984-04-03 1985-10-09 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0160249A2 (en) * 1984-04-28 1985-11-06 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0160249A3 (en) * 1984-04-28 1987-05-27 Ruhrchemie Aktiengesellschaft Process for the preparation of aldehydes
EP0163234A2 (en) * 1984-06-01 1985-12-04 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0163234A3 (en) * 1984-06-01 1987-05-27 Ruhrchemie Aktiengesellschaft Process for the preparation of aldehydes
EP0216151A2 (en) * 1985-08-29 1987-04-01 Hoechst Aktiengesellschaft Process for the preparation of 2-ethyl hexanol
EP0216151A3 (en) * 1985-08-29 1989-03-29 Hoechst Aktiengesellschaft Process for the preparation of 2-ethyl hexanol
EP0226988A2 (en) * 1985-12-24 1987-07-01 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0226988A3 (en) * 1985-12-24 1989-04-12 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0255673A2 (en) * 1986-08-06 1988-02-10 Hoechst Aktiengesellschaft Process for the recovery of rhodium from aqueous solutions containing rhodium complex compounds
EP0255673A3 (en) * 1986-08-06 1990-07-11 Hoechst Aktiengesellschaft Process for the recovery of rhodium from aqueous solutions containing rhodium complex compounds
EP0302375A2 (en) * 1987-08-06 1989-02-08 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0302375A3 (en) * 1987-08-06 1989-05-17 Hoechst Aktiengesellschaft Process for the preparation of aldehydes
EP0372615A2 (en) * 1988-11-28 1990-06-13 Virginia Tech Intellectual Properties, Inc. Hydroformylation process
EP0372615A3 (en) * 1988-11-28 1991-07-17 Virginia Tech Intellectual Properties, Inc. Hydroformylation process
EP0621075A2 (en) * 1993-04-19 1994-10-26 Kuraray Co., Ltd. Novel rhodium-containing catalyst
EP0621075A3 (en) * 1993-04-19 1994-11-09 Kuraray Co Novel rhodium-containing catalyst.
US5434311A (en) * 1993-04-19 1995-07-18 Kuraray Co., Ltd. Rhodium-containing catalyst
BE1008019A3 (en) * 1994-01-07 1995-12-12 Dsm Nv Process for the preparation of an aldehyde.
EP0776880A1 (en) 1995-11-30 1997-06-04 Institut Francais Du Petrole Process for the hydroformylation of olefinic compounds
US6211414B1 (en) 1997-01-13 2001-04-03 Celanese Gmbh Process for preparing aldehydes by hydroformylation
WO1998030527A1 (en) * 1997-01-13 1998-07-16 Celanese Gmbh Process for preparing aldehydes by hydroformylation
EP1160234A1 (en) * 1997-01-13 2001-12-05 Celanese Chemicals Europe GmbH Process for the preparation of aldehydes by hydroformylation
WO1999013982A1 (en) * 1997-09-16 1999-03-25 Celanese Chemicals Europe Gmbh Method for preparing aldehydes by hydroformylation
US6339174B1 (en) 1997-09-16 2002-01-15 Celanese Chemicals Europe Gmbh Method for preparing aldehydes by hydroformylation
EP0924218A1 (en) * 1997-12-22 1999-06-23 Celanese GmbH Non aqueous ionogen liquid ligands, process for their preparation and their use as components for catalysts
US6103908A (en) * 1997-12-22 2000-08-15 Celanese Gmbh Nonaqueous ionic ligand liquids, process for preparing them and their use as catalyst constituents
WO1999060003A1 (en) * 1998-05-20 1999-11-25 Rhodia Fiber And Resin Intermediates Novel furylphosphines and organometallic complexes containing them
FR2778915A1 (en) * 1998-05-20 1999-11-26 Rhone Poulenc Fibres New furylphosphines and derived organometallic complexes, used as biphase catalysts
US6417375B1 (en) 1998-05-20 2002-07-09 Rhodia Fiber & Resin Intermediates Furylphosphines and organometallic complexes containing them

Also Published As

Publication number Publication date
FR2314910B1 (en) 1977-12-02
BE843177A (en) 1976-12-20
JPS57167937A (en) 1982-10-16

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